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methyl 2-(2-dimethylaminovinyl)-5-fluoro-3-nitrobenzoate[ No CAS ]
[ 1082040-43-4 ]
Yield
Reaction Conditions
Operation in experiment
7.1 g
With hydrogen; In methanol; at 40℃; under 7600.51 Torr; for 10h;
step 4:Compound 4 (23.7 g, 0.081 mol) was dissolved in 200 mL of methanol, 2.4 g of Raney nickel catalyst was added, hydrogen gas was introduced, and the reaction was carried out at 40 C for 10 hours under 10 atmospheres. The catalyst was removed by filtration, then 300 mL of water was added, the crude product was obtained by filtration. The crude product was recrystallized from methanol/water to give 7.1 g of yellow solid 6-fluoro-1H-indole-4-carboxylic acid methyl ester.
6-fluoro-3-(2-nitroethyl)-1H-indole-4-carboxylic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50 kg
With 4-tert-Butylcatechol; In toluene; for 24h;Reflux; Industrial scale;
6-fluoro-1H-indazole-4-carboxylic acidAdd methyl ester (60kg) to the reaction vessel, add 2-nitroacetic acid ethyl acetate (60kg,) toluene 720L, p-tert-butyl catechol (3kg), heat reflux, reaction for 24h, the reaction is completed, and most of the solvent is distilled off. The solid was precipitated and suction filtered to give a solid 50 kg.
With triethylsilane; trifluoroacetic acid; In dichloromethane; at 8 - 20℃; for 90h;
2-(1,3-dioxoisoindolin-2-yl)acetaldehyde (2-DAA, i.e., the compound of formula (IX), 191.0 g, 1.3 eq.) and <strong>[1082040-43-4]6-fluoro-1H-indole-4-carboxylic acid methyl ester</strong> (<strong>[1082040-43-4]6-FICAME</strong>, i.e., the compound of formula (6), 150.0 g, 1 eq.) in dichloromethane (CH2Cl2, 997.5 g) was added with triethylsilane (TES, 361.4 g, 4 eq.) and the mixture was stirred at room temperature. A solution of trifluoroacetic acid (TFA, 180.0 g, 2 eq.) in dichloromethane (CH2Cl2, 399.0 g) was added into the above mixture at 8 C. and kept stirring for 2 hours. Afterwards, it was stirred at room temperature for 86 hours and cooled to about 8 C. for another 2 hours. After filtrating, the solid were washed with CH2Cl2 and was added into ethyl acetate (EA). The mixture was heated to reflux for 2 hours and cooled to room temperature. After filtrating, the solids were washed with EA and dried under vacuum to obtain 3-(2-(phthalimido)ethyl)-<strong>[1082040-43-4]6-fluoro-1H-indole-4-carboxylic acid methyl ester</strong> (i.e., the compound of formula (7), 157.16 g, 55%).
With toluene-4-sulfonic acid In methanol at 70℃; for 4h;
1.A
Step A) takes the solid 3-amino-5-fluorobenzoic acid methyl ester that is cheap and easy to obtain as starting material,Using methanol as solvent, under the catalysis of protonic acid p-toluenesulfonic acid and pyruvic acid under reflux conditions, rearrangement and deacidification also occur,Through cooling and crystallization, filtration or centrifugation, the indole compound of solid 2 is obtained, and the concrete steps are as follows:Add 3-amino-5-fluorobenzoic acid methyl ester (169g, 1mol) in the four-necked reaction flask of thermometer 1LPyruvic acid (105.6g, 1.2mol) solvent methanol 338g, under stirring, add the catalytic amount of p-toluenesulfonic acid 3.38g,The oil bath was heated to 70°C, the reaction was refluxed for 4h, and the reaction was monitored by TLC.The compound 185g of wet weight solid 2 was obtained by filtration, 168.8g after drying, yield: 87.5%
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